


Pretty

by TheLittleRedWhoCouldWrite



Series: SPN Kink Bingo 2018 [12]
Category: Supernatural
Genre: Bottom Sam, Clothes Sharing, F/M, Femdom, Light BDSM, Pegging
Language: English
Status: Completed
Published: 2018-11-30
Updated: 2018-11-30
Packaged: 2019-09-02 14:57:20
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,451
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16789213
Author URL: https://archiveofourown.org/users/TheLittleRedWhoCouldWrite/pseuds/TheLittleRedWhoCouldWrite
Summary: Jess takes care of her boySquare filled: Clothes sharing





	Pretty

Sam closes the apartment door with a sigh, dropping his bag beside it and kicking off his shoes.

“Rough day?” Jess asks.

Sam turns to look at her and inhales sharply at what he sees.

Jess is leaning against the doorway to their bedroom, dressed in nothing but one of his flannel shirts and a pair of heels that make her legs look a million miles longer than they usually do. It hangs loosely on her slim frame, left open to reveal her body and the dildo in the black harness on her hips.

“Oh,” Sam breathes, shifting to try and relieve the pressure quickly building in his jeans.

“Oh?” she echoes with a lifted eyebrow, levering herself off the doorframe and beginning a slow walk towards him.

“Hi,” he manages.

Jess laughs and he relaxes a little. She wraps her arms around his waist, hands sliding under the waistband of his jeans and into his boxers. He bites his lip when she grabs his ass, hands flying to her hips.

“Hello,” Jess purrs, lifting her chin to kiss him. Her strapon pokes his hip and Sam can’t suppress a whimper. “I know just the thing to make your day better. Come to bed?”

“Happily,” Sam replies.

She gives his ass a squeeze and then steps away, tugging gently on the front of his shirt as she goes. Her heels click on the hardwood and Sam licks his lips, eyeing the way her body moves as she leads him into the bedroom.

“Strip for me, baby,” she orders, stopping by the bed.

Sam doesn’t hesitate. He begins to strip at the speed of light but stops when she shakes her head.

“Slowly,” Jess reminds him. “You know that.”

He blushes but obeys. He takes his time, drawing his shirt over his head. Jess watches with hungry eyes as he toes off his socks and then slowly slides his jeans down, revealing the blue lacy thing he snitched from her drawer that morning. Jess grins wickedly.

“Beautiful,” she murmurs, reaching her hand out to him.

Sam takes it, letting her draw him in close once more. Her fingers slide into his hair and she just looks at him a moment.

“I want you on your back on the bed,” she decides.

He obeys, stretching his body out on the sheets. Jess runs a hand up his thigh, skirting his cock where it presses against the confines of the lace to continue across his abs and stopping in the center of his best.

“You want this, don’t you?” she says, her other hand lazily stroking the dildo like it’s a real cock.

Sam nods, gazing up at her, and she smiles.

“Good.”

Jess crawls up onto the bed and straddles his chest. The dildo knocks against his lips, but Sam doesn’t move.

“Good boy,” she praises, running her thumb over his lips before gently pushing it between. He sucks on the intrusion, keeping his eyes on her face. “Fuck, baby. How can someone look so damn good?”

Sam hums softly, scraping his teeth lightly against the pad of her thumb. She removed the digit, almost reluctantly, and taps the head of the dildo against his lips.

“Open up.”

He does, allowing her to guide it in. The toy is silicone and one of the biggest in their collection. His jaw protests a little against the stretch, but he just focuses on relaxing the muscles and letting Jess control the depth. She doesn’t push too far past the head, which Sam is grateful for. He focuses his attention on it, sucking and licking like he’s seen Jess do to his own cock.

“Pretty,” she coos, petting his hair.

Sam’s eyes flutter closed. He digs his fingers into the sheets, fighting the urge to touch himself. Jess notices. She pulls away, swinging herself off his body, and moves lower. She settles on his thighs, gently grinding the dildo against his cock through the lace.

“So needy,” Jess observes when he tries to roll his hips against the toy. “You want this, don't you?” She grips his cock through the lace and rubs her fake one against it. “My pretty boy wants my cock, isn't that right?”

He nods almost frantically, forcing himself to take deep, even breaths.

“Use your words, Samuel.”

He shivers at the use of his full name. “I… I want your cock.”

“Where?” she prompts. “Between those sinful pink lips?” Jess leans down to bestow a kiss upon said lips before her hands drift around to grip his ass, pulling the cheeks apart and massaging them. “Or here, in that tight little hole?”

Sam has to bite his cheek and curl his fingers so tightly into the sheets that he can feel his fingernails in his palm through the fabric, otherwise he's going to cum without ever being touch.

“Oh, I see,” Jess chuckles, nudging at the panties until the lace slips between his cheeks and rubs against his hole in a way that shouldn't be pleasant, but is. “Tell me, baby. Tell me what you need.”

“Please,” he manages. “Please, I want it… I want it… in my ass.”

“Hmm, that's not what I was looking for and you know it.”

Sam's face is on fire and he really wishes he was on all fours so he could hide in the pillow. “I want… yourcockinmytightlittlehole.”

The words come out all at once, tripping over each other in their haste.

“I didn't quite catch that.” Jess tugs at the waistband of the panties, drawing them even tighter against his hole.

Sam whimpers and forces himself to slow his words down. “I want your cock in… fuck,  _ Jess _ … in my tight little hole.”

Jess grins from where she’s sucking on one nipple and stretches up to kiss him. “Good boy.” Her weight vanishes from his thighs and she gives his hip a light smack. “Roll over, Sam. Wanna see that ass.”

Sam is quick to obey, rolling onto all fours. He lowers he chest to the mattress, pillowing his head on his folded arms, and Jess groans, shedding her heels.

“Fucking perfect.” Her hand runs over the curve of his ass. Sam hears the cap of the lube- when she grabbed that, he has no clue- and then she yanks the panties down. “Gonna take good care of you.”

Slick, slender fingers press against his hole, gently massaging the muscle until he relaxes. She presses two in without any more hesitation and Sam groans.

“Easy.” Jess's voice is hardly more than a breath, hot against the small of his back.

She crooks her fingers against his prostate and grins into his skin. A few twists, massaging the muscles into relaxation, and Jess sits up with a pleased sound. She pulls her fingers free and Sam feels the cool, slick tip of the toy against his hole.

“Bear down,” she says, like he hasn't done this dozens of times. Sam obeys and the thick head pops past the ring of muscle. Jess soothes his whine with a hand down his spine, even as she drives in deeper without any hesitation.

“ _ Jess _ .” It feels like her cock is in his chest, choking his words.

“Yeah,” is the only reply as Jess digs his fingers into his waist and starts fucking him with all the power behind those perfect hips. Sam muffles his shouts of pleasure into the pillow, bracing himself against the headboard with one hand as the other hand reaches back to cover Jess's on his waist.

She doesn't hold back, focusing on fucking him into the mattress. Sam lets her, more than happy to have her lean, soft body blanketing his when his legs give out and he ends up sprawled out on the bed. She’s still wearing his flannel and Sam can feel a few buttons digging into his spine. Jess bites and kisses along his upper back and shoulders. Sam shudders and grips at the sheets, fighting the urge to search for more friction on his cock.

Jess senses what's on his mind and one hand worms its way between Sam's hips and the mattress, slender fingers curling around his cock. A few well-placed thrusts of her body, a few strokes topped by her thumb over his slit, and Sam is spilling onto the sheets with a moan. Jess fucks him through it, murmuring soothing words against a bite mark.

She rolls him onto his side, smaller body spooning up against his back and the toy still in his hole. There, with soft hands petting his hair and soft lips on his shoulder and soft, soft flannel warming his skin and that hard, unforgiving toy in his ass, Sam falls asleep.


End file.
